The Apprentice – part 8

Miss Thornton had said that she’d be inviting me to her apartment, and today she did. Not much notice since she wanted me there this evening. I got to her place a little after seven and she let me in. She was dressed as a nun, which amused and intrigued me. She’s really into costumes.

“Does this outfit excite you?” she asked as I sat on the couch.

“It’s very fetching,” I said. “If I had been a Catholic, I suppose it might have been one of my boyhood fantasies. Punished by a nun. Are you going to punish me?” I smiled.

“Yes, I am,” she said matter-of-factly. “Very severely. I want you to undress now.” She stood near me as I took off my clothes one item at a time, and soon I was standing in front of her stark naked with my cock standing up and out in front of me. Her eyes sparkled as she looked at it, but she said “that’s a nasty thing you have there. I’m going to have to do something about it. Come into the bedroom, now.” I started down the hall and she grasped my neck and marched me like a bad boy going to the principal’s office.

In the bedroom, she indicated that I should get on the bed. “Face down,” she said. I complied, and she came to the side and lifted a piece of material from the floor and tied my wrist. Then she went around the bed and did the same to the other wrist. I looked back at her and saw that she had a pretty good sized whip in her hand, which she brought down on my backside. “Ow!” I yelled. “That really hurt.”

“Good. Punishment is supposed to hurt.” And she hit me with the thing again. She used it on me five or six more times, and to my amazement my cock was even bigger pushing into the bed- clothes than it had been. I’ve heard that such activities can be arousing, but I never would have believed it. Whack! She hit me again.

Then she walked around and freed one of my wrists. “Turn over,” she said, and I rolled on to my back. My cheeks were smarting with pain, and my cock was standing straight up. “You are still being bad,” she said, and moved around the bed to secure my wrists the opposite way. God, I thought, she’s not going to whip me there, is she?

She raised the weapon as if to bring it down on my cock, and then stopped. “I must cause that disgusting thing to go away. Whipping you only seems to excite you. You are truly evil. I see I must resort to other methods.”

“What other methods? Sister?” I added, which obviously pleased her. She wanted me to really participate in her fantasy.

“I know from my experience with other evil boys that that disgusting thing will shrivel and go away if you shoot your vile fluid from it. So I’m going to make you do that. But don’t think that you won’t taste this whip again some time in the future.”

“Oh no, sister, not the whip please. And I don’t want you to force the fluid from me. Please, please,” I pleaded.

“Be quiet! You don’t have any choice. And you have no idea what a sacrifice this is for me to make.” She knelt on the bed and reached between my legs to grasp my balls. She squeezed them, hard, and I whimpered.

“Oh, that hurts,” I moaned.

“Of course it does. Pain will make you pure.” She continued to squeeze me, hovering over my cock and looking down at it as though it was supposed to be draining already. “You are more evil than the others. It isn’t responding. My sacrifice must increase.” And she lowered her head onto my tool.

I got very excited, by the game and by the sight of a woman in full nun’s dress going down on me. Her cowl and her wimple looked genuine, and the large cross swinging in front of her added a really authentic touch. Her mouth closed around me, and she began sucking up and down, still squeezing my balls very hard. “Mmnnnn, sister,” I moaned. “I want to rid myself of this evil substance. I can’t hold back. Please don’t stop,” and as she continued to suck me I felt the climax starting in my belly and sweeping over my loins. I shot into her mouth, and she continued to suck me while my balls drained completely. Then my cock started to shrivel, and she looked up triumphantly.

“Ha! It worked again. Goodness has triumphed over evil.” She looked as though she really believed what she was saying, rather than acting, and I decided that it meant she was a truly great actress. Now she crawled up the bed over me, pulling up the voluminous black garment she was wearing. She got over my face, and I was staring into the hairy slit between her legs.

“Sister, you ain’t got no underwear on,” I joked.

“Silence! This is not a joke. You are now to remove the evil from me. Put your mouth on my disgusting slit, and lick me.”

I obeyed, and she clutched at my head, her eyes closed. She rocked back and forth on my face, and I pushed my tongue as far into her as I could. My upper lip felt her large clit pushing against it, and I moved my mouth to start sucking her. She moaned with pleasure, and came in a flood of juice which nearly gagged me lying on my back. But I licked and slurped at her gushing pussy until I had taken in most of her discharge. She let go of my head, and said “Now we are both purified.”

“Is that good for life, sister?” I asked innocently.

“Of course not. Evil always creeps back. We may have to do this quite often in order to triumph over it.”

“Well, I’m against evil. I’ll do whatever you require.”

“You are a good boy. Are you sure you’re not Catholic?” And we both laughed. After she untied my wrists, I sat on the edge of the bed. From the open closet door, a small red light was glowing, and I realized that she had taped the entire thing. I hope she gives me a copy.

I went home shortly after that. There was no hope of my getting it up again tonight, since she had really drained the evil out of me. She had gotten out of the nun’s outfit, and was wearing a robe. She kissed me at the door, and said “Come back soon.”

12

I was in heaven, what with a good job that I really liked and all the sex anyone could ask for. I was faintly disturbed by the homosexual stuff, and by the fact that I enjoyed it so much, but I chalked the whole thing up to gaining experience. I sure hope no one ever spreads tales, though.

But spreading tail is okay, and I’m amazed by how many women like it in the ass. When I was in high school and the guys would sit around talking, we dreamed of doing such things; but I never really thought I’d get to do them. With all the lying that went on back then, nobody ever claimed to have done that. Of course, if I were with them today, I probably wouldn’t tell anyone either; so maybe some had done it but didn’t want to say anything. Nah . . . not that bunch. If one of them had had a woman or a girl that way, we would have heard about it. In stunning detail.

So, women like it in the ass. But while I’d seen a lot of it, I hadn’t gotten much. Not Ms. Gray, or Ms. Thornton, or Ginny, or Mrs. Barrett. It gives me something to look forward to, and I can add them to Wendy and Heather and Marianne. So many women, so little time.

And so many men, too. I confess that I like doing it to men and having them do it me. When I’m being fucked there, I feel absolutely dependent on the man hunched over my back and absolutely at his mercy. And it feels . . . good. I wonder if women feel that way when a truly powerful man is ploughing them; the sense that, since you can’t control what’s happening to you, you have to rely on the other person to take care of you.

I guess the fact that I like it makes me a homosexual, but that’s just a label. I think of it as just another way to express sexuality, and I expect to be doing it for a long time. Perhaps when I’m a lot older, when women no longer find me attractive, I’ll concentrate on men. It’s horri
fying to think that someday I won’t be able to turn a woman on, but it’s a long way off and will have to take care of itse
lf. In the meantime, there is a lot of pussy around, and I mean to get my share.

Quite often, Ms. Thornton would call me up to her office, where the boss never seemed to be. She would have me sit in the big chair in his office, and she would kneel between my legs and slowly remove my cock from my pants. Every time, it was huge by the time she got it out. Her mouth was soft and loving, and she was very attentive to my organ. She would fondle it, and lick it, and stroke it with her fist, and then she would take it in her mouth and suck it until I burst into her mouth. I could fill it up very easily, since I seemed to be manufacturing a great deal of semen these days. I guess letting it fly causes more to be produced right away.

Once or twice after she did that, I went down on her in the same chair, with her scrambling to get her panties off and pull my face into her yearning snatch. We didn’t always do that, however; I guess she had an appointment, or she expected the boss to come back, or something. But the times she had me do it, she moaned and gushed heavily as she came in my face.

I was seeing Heather once a week, at her place, and all in all I was getting a little exhausted. The idea that I might need some relief was starting to occur to me, and just at that time, I got it. There was a new guy working in the company, whose name was Walt; he hadn’t been invited to any of the company fun and games, but I know that he knew about them from conversations we had at lunch. He tried to pump me about my own involvement, but I was coy and didn’t tell him anything. He was a good-looking guy, and I knew it wouldn’t be long before one of the women in the company went after him. Or one of the men, if he was game.

Ms. Thornton asked me about him once or twice, but I told her I didn’t know much about him. Ms. Gray did also, and I gave her the same answer. Then one Thursday Ms. Gray stopped me in the hall and told me she’d like me to come by her apartment on Saturday. “There’ll be somebody new there, but you don’t mind I take it?”

“Not at all. What time?” She told me 10 a.m., and we both went back to work. That afternoon, I saw Walt studying me, and wondered if he was the new person who would be at Olivia’s.